Nitrogen → 6-(Pyridin-4-yl)-[1]pyrindin-5,7-dione

HRID 49910

Reaction equation

HRID 49910 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]2[C:7](=[O:10])[O:8][CH2:9][C:2]=12.[N:11]1[CH:16]=[CH:15][C:14]([CH:17]=O)=[CH:13][CH:12]=1.C[O-].[Na+].N#N>CO.C(OCC)(=O)CC.O>[N:11]1[CH:16]=[CH:15][C:14]([CH:17]2[C:9](=[O:8])[C:2]3[N:1]=[CH:6][CH:5]=[CH:4][C:3]=3[C:7]2=[O:10])=[CH:13][CH:12]=1

Participants

8

Reactant 4

HCID 947NitrogenHCID 133894-PyridinecarboxaldehydeHCID 819439furo(3,4-b)pyridin-5(7H)-oneHCID 10942334Sodium Methoxide

Product 1

HCID 862046506-(Pyridin-4-yl)-[1]pyrindin-5,7-dione

Reagents, catalysts & solvents 3

HCID 887MethanolSolvent2×HCID 962WaterSolventHCID 7749Ethyl PropionateSolvent

Procedure

To a suspension of 20.27 g (150 mmol) furo[3,4-b]pyridin-5(7H)-one (for preparation see Synthesis 1997, 113) and 14.13 ml (150 mmol) 4-pyridinecarbaldehyde in 120 ml methanol and 75 ml ethyl propionate, 27.8 ml (150 mmol) of a 5.4 M solution of sodium methylate in methanol is added dropwise under ice cooling (and N2 atmosphere). The mixture is heated for 15 min to RT and then for 2 h to reflux temperature. The suspension temporarily goes into solution before a solid forms again. After cooling, 120 ml water is added, before stirring, filtering and washing the product with water. Further product is obtainable from the filtrate by acidification with acetic acid: FAB MS (M+H)+=225.

Workup

  1. temperatureThe mixture is heated for 15 min to RT
  2. temperaturefor 2 h to reflux temperature
  3. temperatureAfter cooling
  4. filtrationfiltering
  5. washwashing the product with water

Sources & evidence

ORD record
ord-56b0e90b53f24975b41a3d0d8eef69c9
Source dataset
uspto-grants-2004_03
Patent number
US06710047B2

Linked notes

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